Ethyl bromoacetate → HCID 69288747, compound

HRID 1247253Notes

Reaction equation

HRID 1247253 reaction equation
[C:1]([C:3]1[CH:24]=[CH:23][C:6]([CH2:7][NH:8][C:9](=[O:22])[CH:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([OH:21])[CH:14]=2)[O:11][CH3:12])=[CH:5][CH:4]=1)#[N:2].C([O-])([O-])=O.[K+].[K+].Br[CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34]>CN(C=O)C.CCOC(C)=O>[CH2:36]([O:35][C:33](=[O:34])[CH2:32][O:21][C:15]1[CH:14]=[C:13]([CH:10]([C:9](=[O:22])[NH:8][CH2:7][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:24][CH:23]=2)[O:11][CH3:12])[CH:18]=[CH:17][C:16]=1[O:19][CH3:20])[CH3:37]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 21905311HCID 21905311, compound

Product 1

HCID 69288747HCID 69288747, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (RS)-N-(4-cyano-benzyl)-2-(3-hydroxy-4-methoxy-phenyl)-2-methoxy-acetamide (0.303 g) at rt in DMF (3 ml) were added K2CO3 (0.14 g) and ethyl bromoacetate (0.169 g). The reaction mixture was then stirred at rt under an argon atmosphere for 5 h 45. The mixture was diluted with EtOAc (25 ml), washed with water (25 ml) and brine (25 ml), dried (MgSO4), filtered and concentrated (rotavapor) to leave the crude product as a light yellow gum. The product was purified by chromatography (Silicagel (20 g) using a gradient profile: cyclohexane to cyclohexane/EtOAc 35:65) to give (RS)-{5-[(4-cyano-benzylcarbamoyl)-methoxy-methyl]-2-methoxy-phenoxy}-acetic acid ethyl ester (0.342 g) as a white solid.

Workup

  1. washwashed with water (25 ml) and brine (25 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated (rotavapor)
  5. customto leave the crude product as a light yellow gum
  6. customThe product was purified by chromatography (Silicagel (20 g)

Sources & evidence

ORD record
ord-01f862ece48f4cdeadb4cdcd85578757
Source dataset
uspto-grants-2006_10
Patent number
US07129238B2

Reaction notes

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